Lithium amide

Lithium amide or lithium azanide is an inorganic compound with the chemical formula LiNH2. It is a white solid with a tetragonal crystal structure. Lithium amide can be made by treating lithium metal with liquid ammonia:[1]

2Li + 2NH3 → 2LiNH2 + H2
Lithium amide

__ Li+      __ N3−      __ H+
Names
IUPAC name
Lithium amide
Other names
Lithamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.029.062
UNII
Properties
LiNH
2
Molar mass 22.96 g/mol
Appearance white solid
Density 1.178 g/cm3
Melting point 375 °C (707 °F; 648 K)
Boiling point 430 °C (806 °F; 703 K) decomposes
reacts
Solubility slightly soluble in ethanol
insoluble in ammonia
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298)
 -182 kJ/mol
Hazards
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
1
3
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Other lithium amides

The conjugate bases of amines are known as amides. Thus, a lithium amide may also refer to any compound in the class of the lithium salt of an amine. These compounds have the general form Li<NR2, with the chemical lithium amide itself as the parent structure. Common lithium amides include lithium diisopropylamide (LDA), lithium tetramethylpiperidide (LiTMP), and lithium hexamethyldisilazide (LiHMDS). They are produced by the reaction of Li metal with the appropriate amine:

2Li + 2R2NH → 2LiNR2 + H2

Lithium amides are very reactive compounds. Specifically, they are strong bases.

Examples

Lithium tetramethylpiperidide has been crystallised as a tetramer.[2] On the other hand, the lithium derivative of bis(1-phenylethyl)amine crystallises as a trimer:[3]

Tetrameric lithium tetramethylpiperidide
Trimeric lithium bis(1-phenylethyl)amide

It is also possible to make mixed oligomers of metal alkoxides and amides.[4] These are related to the superbases which are mixtures of metal alkoxides and alkyls. The cyclic oligomers form when the nitrogen of the amide forms a sigma bond to a lithium while the nitrogen lone pair binds to another metal centre.

Other organolithium compounds (such as BuLi) are generally considered to exist in and function via high-order, aggregated species.

See also

References
  1. P. W. Schenk (1963). "Lithium amide". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. 1. NY,NY: Academic Press. p. 454.
  2. M.F. Lappert; M.J. Slade; A. Singh; J.L. Atwood; R.D. Rogers; R. Shakir (1983). "Structure and reactivity of sterically hindered lithium amides and their diethyl etherates: crystal and molecular structures of [Li{N(SiMe3)2}(OEt2)]2 and tetrakis(2,2,6,6-tetramethylpiperidinatolithium)". Journal of the American Chemical Society. 105 (2): 302–304. doi:10.1021/ja00340a031.
  3. D.R. Armstrong; K.W. Henderson; A.R. Kennedy; W.J. Kerr; F.S. Mair; J.H. Moir; P.H. Moran; R. Snaith (1999). "Structural studies of the chiral lithium amides [{PhC(H)Me}2NLi] and [PhCH2{PhC(H)Me}NLi·THF] derived from α-methylbenzylamine". Dalton Transactions: 4063–4068. doi:10.1039/A904725E.
  4. K.W. Henderson, D.S. Walther & P.G. Williard (1995). "Identification of a Unimetal Complex of Bases by 6Li NMR Spectroscopy and Single-Crystal Analysis". Journal of the American Chemical Society. 117 (33): 8680–8681. doi:10.1021/ja00138a030.
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